2051-90-3Relevant academic research and scientific papers
An expedient one-pot synthesis of benzophenone Schiff bases from benzene
Akhrem, Irena S.,Afanas'eva, Lyudmila V.,Avetisyan, Dzhul'etta V.,Artyushin, Oleg I.,Kagramanov, Nikolai D.
, p. 238 - 240 (2020/05/25)
A simple and efficient one-pot synthesis of benzophenone Schiff bases from benzene, CCl4 and aromatic amines was developed based on the the reaction of benzene with CCl4·AlCl3 complex. This method affords Ph2CCl2 as well as the products of its subsequent reaction with aromatic amines, benzophenone Schiff bases, selectively and in good yields.
A crystallographic and spectroscopic study on the reactions of WCl 6 with carbonyl compounds
Dolci, Sara,Marchetti, Fabio,Pampaloni, Guido,Zacchini, Stefano
, p. 5635 - 5648 (2013/06/05)
WCl6, 1, reacted with two equivalents of HC(O)NR2 (R = Me, Et) in CH2Cl2 to afford the W(vi) oxo-derivatives WOCl4(OCHNR2) (R = Me, 2a; R = Et, 2b) as main products. The hexachlorotungstate(v) salts [{OC-N(Me)CH2CH2CH 2}2(μ-H)][WCl6], 3, and [PhNHC(Me)N(Ph)C(O) Me][WCl6], 4, were isolated in moderate yields from the 1:2 molar reactions of 1 with N-methyl-2-pyrrolidone (in CH2Cl2) and acetanilide (in CDCl3), respectively. The additions of two equivalents of ketones/aldehydes to 1/CH2Cl2 yielded the complexes WOCl4[OC(R)(R′)] (R = Me, R′ = Ph, 5a; R = R′ = Ph, 5b; R = R′ = Me, 5c; R = R′ = Et, 5d; R = H, R′ = 2-Me-C6H4, 5e) and equimolar amounts of C(R)(R′)Cl2. Analogously, WOCl3[κ2- {1,2-C6H4(O)(CHO)}], 5f, and 1,2-C6H 4(OH)(CHCl2) were obtained from 1 and salicylaldehyde. The 1:1 reaction of 1 with acetone in CH2Cl2 resulted in the clean formation of WOCl4 and 2,2-dichloropropane. Compounds 5a,b,f were isolated as crystalline solids, whereas 5c,d,e could be detected by solution NMR only. The interaction of 1/CH2Cl2 with isatin, in a 1:1 molar ratio, revealed to be a new, convenient route for the synthesis of 3,3-dichloro-2,3-dihydro-1H-indol-2-one, 6. The 1:1 reactions of 1 with R′OCH(R)CO2Me (R = H, R′ = Me; R = Me, R′ = H) in a chlorinated solvent afforded the tungsten(v) adducts WCl 4[κ2-OCH(R)CO2Me] (R = H, 7a; R = Me, 7b). 1/CH2Cl2 reacted sluggishly with equimolar quantities of trans-(CO2Et)CHCH(CO2Et) and CH2(CO 2Me)2 to give, respectively, the W(iv) derivatives WCl4[κ2-CH2(CO2Me) 2], 8a, and [WCl4-κ2-{trans-(CO 2Et)CHCH (CO2Et)}]n, 8b, in about 70% yields. The molecular structures of 2a, 3, 4, 5a, 5f, 7a and 7b were ascertained by X-ray diffraction studies.
METHOD FOR PREPARING ALIZARIN DERIVATIVE COMPOUND, NOVEL ALIZARIN DERIVATIVE COMPOUND, SURFACE MODIFICATION METHOD, PHOTOELECTRIC CONVERSION FILM, PHOTOELECTRIC CONVERSION ELEMENT, AND ELECTROPHOTOGRAPHIC PHOTORECEPTOR
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Page/Page column 50, (2011/06/26)
The present invention provides a novel alizarin derivative compound and a simplified and low cost method for preparing an alizarin derivative compound including: obtaining a compound represented by Formula (2) using a compound represented by Formula (3); and obtaining an alizarin derivative compound represented by Formula (1) using the compound represented by Formula (2); in Formulae (1) to (3), R1 represents a hydrogen atom or a substituent; n represents an integer of 1 to 3, L represents a specific alkyl group; Q represents an atomic group needed to form an aromatic ring or a heteroaromatic ring with adjacent carbon atoms; and P represents an atomic group which includes an atom(s) selected from a hydrogen atom, a carbon atom, an oxygen atom, a sulfur atom, a silicon atom and a boron atom, and which is needed to form a ring structure group with adjacent two oxygen atoms and two carbon atoms; Formula (1) Formula (2) Formula (3).
A mild synthesis of vinyl halides and gem-dihalides using triphenyl phosphite-halogen-based reagents
Spaggiari, Alberto,Vaccari, Daniele,Davoli, Paolo,Torre, Giovanni,Prati, Fabio
, p. 2216 - 2219 (2007/10/03)
A new application of (PhO)3P-halogen-based reagents to the synthesis of vinyl halides and gem-dihalides is described. Vinyl halides were prepared in good to excellent yields from enolizable ketones, whereas aldehydes afforded the corresponding gem-dihalides. The halogenation proceeded smoothly under mild conditions.
2-Aminoethoxydiphenyl borate as a prototype drug for a group of structurally related calcium channel blockers in human platelets
Dobrydneva, Yuliya,Abelt, Christopher J.,Dovel, Beth,Thadigiri, Celina M.,Williams, Roy L.,Blackmore, Peter F.
, p. 247 - 256 (2007/10/03)
We have synthesized a series of 2-aminoethoxydiphenyl borate (2-APB, 2,2-diphenyl-1,3,2-oxazaborolidine) analogs and tested their ability to inhibit thrombin-induced Ca2+ influx in human platelets. The analogs were either synthesized by adding various substituents to the oxazaborolidine ring (methyl, dimethyl, tert-butyl, phenyl, methyl phenyl, and pyridyl) or increasing the size of the oxazaborolidine ring to seven- and nine-membered rings. NMR analysis of the boron-containing analogs suggests that each of them exist as a ring structure through the formation of an N→B coordinate bond (except for the hexyl analog). The possibility that these boron-containing compounds formed dimers was also considered. All compounds dose-dependently inhibited thrombin-induced Ca2+ influx in human platelets, with the 2,2-diphenyl-1,3,2-oxazaborolidine-5-one derivative having the weakest activity at 100 μM, whereas the (S)-4-benzyl and (R)-4-benzyl derivatives of 2-APB were approximately 10 times more potent than the parent 2-APB. Two nonboron analogs (3-methyl and 3-tert-butyl 2,2-diphenyl-1,3-oxazolidine) were synthesized; they had approximately the same activity as 2-APB, and this implies that the presence of boron was not necessary for inhibitory activity. All of the compounds tested were also able to inhibit thrombininduced calcium release. We concluded that extensive modifications of the oxazaborolidine ring in 2-APB can be made, and Ca2+-blocking activity was maintained. Copyright
Natural bentonite clay/dilute HNO3 (40%) - A mild, efficient, and reusable catalyst/reagent system for selective mono nitration and benzylic oxidations
Bahulayan, Damodaran,Narayan, Gopinathan,Sreekumar, Vellalath,Lalithambika, Malathy
, p. 3565 - 3574 (2007/10/03)
Selective mono nitration of Aromatic hydrocarbons and benzylic oxidations can be achieved in high yield using reusable catalyst/reagent system consisting of bentonite clay and dilute HNO3 under relatively mild experimental conditions. The dual behavior of the catalyst reagent system is utilized for the regioselective synthesis of a variety of industrially important compounds.
Selective preparation of 4,4′-dichlorodiphenylmethane over zeolite K-L catalyst using sulfuryl chloride
Kale,Singh
, p. 399 - 411 (2008/10/08)
The liquid phase chlorination of diphenylmethane (DPM) to 4,4′-dichlorodiphenylmethane (4,4′-DCDPM) is investigated at 333 K, under atmospheric pressure over a number of zeolite catalysts using sulfuryl chloride (SO2Cl2) as the chlorinating agent. The results obtained are compared with those over the conventional Lewis acid catalyst, AlCl3 as well as without any catalyst. Zeolite K-L is found to be highly active and selective catalyst for the conversion of DPM to 4,4′-DCDPM. The conversion of DPM, rate of DPM conversion and the selectivity (4,4′-DCDPM/2,4′-DCDPM isomer ratio) over zeolite K-L after 1 h of reaction time are found to be 96.8 wt.%, 19.1 mmol g-1 h-1 and 7.4, respectively. The influence of solvent, catalyst concentration, reaction temperature, DPM/SO2Cl2 molar ratio, recycle of zeolite K-L, etc. are also examined. 1,2-Dichloroethane is the best solvent and gives the highest selectivity for 4,4′-DCDPM (4,4′-DCDPM/2,4′-DCDPM isomer ratio = 9.7) with zeolite K-L at 353 K after 1 h of reaction time. The formation of 4,4′-DCDPM is favoured by increase in catalyst concentration, reaction temperature and higher concentration of SO2Cl2 (lower DPM/SO2Cl2 molar ratio). In all these cases, the yield of 4,4′-DCDPM increases with a decrease in the yield of 4-CDPM which suggests that the formation of 4,4′-DCDPM takes place by the consecutive reaction of 4-CDPM. Higher SiO2/Al2O3 ratio (obtained by HCl treatment) of zeolite K-L decreases the conversion of DPM. A noticeable decrease in the activity and selectivity of zeolite K-L is observed on recycling, probably due to reduced crystallinity as well as extraction of small amounts of Al+3 and K+ ions by the HCl, generated in the reaction. Mechanistically, SO2Cl2 is first decomposed into SO2 and Cl2 the latter being polarized by the zeolite catalyst to an electrophile (Cl+) which then attacks the DPM and subsequently produce the monochlorodiphenylmethane (MCDPM). The MCDPM further is attacked by the electrophile (Cl+) and result in the formation of DCDPM.
Hexamethylphosphoramide Catalyzed Conversion of Carbonyl Compounds into geminal-Dichlorides with Thionyl Chloride
Khurana, J. M.,Mehta, Sanjay
, p. 1128 (2007/10/02)
α, β-Unsaturated and aromatic aldehydes can be converted into geminal-dichlorides quantitatively by reaction with thionyl chloride in the presence of catalytic amounts of hexamethylphosphoramide at room temperature
Diaryldichlorocarbonyl Ylides Derived from Dichlorocarbene and Aromatic Ketones
Martin, Charles W.,Gill, Harpal S.,Landgrebe, John A.
, p. 1898 - 1901 (2007/10/02)
The thermal decomposition of phenyl(bromodichloromethyl)mercury (4) in the presence of benzophenone (2) in dry benzene at 80 degC resulted in α-chlorodiphenylacetyl chloride (6) as the only major initial product together with small amounts of dichlorodiphenylmethane (5) and carbon monoxide.Analogous products were observed from fluorenone (3).Dimethyl acetylenedicarboxylate (15) failed to trap the presumed intermediate dihalocarbonyl ylide from either ketone.Attempts to explain the difference in behavior between dihalocarbonyl ylides derived from benzaldehydes and diaryl ketones suggest that in the latter case a twist in the plane of the ylide caused by endo,endo interactions of a chlorine and an aromatic ring leads to rapid closure to oxirane 11 followed by rearrangement to acid chloride 6.Alternative explanations are also explored.
